Polyoxins antifungal activity

A group of aminoacylamino- nucleoside antibiotics (more than 25 components) from cultures of Streptomyces tendae, see also polyoxins. The N. exhibit acar-icidal, insecticidal, and antifungal activities. The activity is based on an inhibition of chitin biosynthesis as a result of the structural analogy to UDP-Al-acetyl-... 

Nucleoside antibiotics with a bicyclic carbohydrate unit from Streptomyces cacaoi var. asoensis. Distinctions are made between O. A (pK i 3.0 pKj2 4.3 pKg3 9.4), O. B, and O. C(pK, 3.1 pK 24.5 pK,j 9.9). 0. represent a large group of polyoxin-like antibiotics with antifungal activities. 

The discovery of the polyoxin group (1) of antifungal nucleoside antibiotics (2) spurred the attention of synthetic chemists as well as biologists for a number of reasons. Their unusual structural features combined with unique biological activity fostered studies on many fronts (3). During their studies on the biosynthesis of the polyoxins, Isono, Crain and McCloskey (4) discovered three novel acidic nucleosides which they called octosyl acid A, B and C,... 

The NCA 138 represents the amino-protected and carboxy-activated form of poly-oxamic acid 140, the hydroxylic amino acid portion of the antifungal family of polyoxins 139, Fig. 8. Other polyolic NCAs such as 141,142, and 143, Fig. 9, have also been prepared from the corresponding a-hydroxy p-lactams with equal success [123, 124]. 

Staake M, Chauhan J, Zhou D, Shanker A, Chatteijee AD, Das S, Patterson SE. Phosphouoxius III synthesis of a-aminophosphonate analogs of antifungal polyoxins with anti-giardia activity. Org. Lett. 2010 12 45%-4599. 

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